


10 Things I (don't) Hate About You

by orphan_account



Category: Supernatural
Genre: Au- 10 things I hate about you, F/M, Fluff, I'm a mess good luck reading this, M/M, ah yes the au nobody asked for but I made anyways, first fanfiction lets do this!
Language: English
Status: In-Progress
Published: 2018-05-20
Updated: 2018-06-25
Packaged: 2019-05-09 07:29:58
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 13,017
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14711768
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: New in town Jessica Moore is instantly smitten with sweet-natured Sam Winchester. Too bad everyone knows Sam can't date, at least not until his flirty but unattainable older brother Dean does. Fortunately for Jess, her newfound best friend Gabriel has a rich jerk of a brother, a loner cousin in desperate need of a social life, and a plan revolving around weekly payments and questionable morals. Now all they need is Dean to fall for Castiel before prom. Sounds easy enough...Right?





	1. Part 1

**Author's Note:**

> Hello and welcome to your average supernatural/10 things I hate about you au. I'm definitely not going to try to explain everyone's names, please have mercy and accept that there could be a high school in Lawrence Kansas where kids run around with names like Lucifer and Castiel. I do bounce between perspectives so I'm sorry if that's confusing, it's mostly Dean and Jess with a few Castiels. Enjoy!

The office buzzes with activity; students arriving late, students sent away by exhausted teachers, teachers who need a break and probably a larger salary. It's altogether overwhelming and Jess finds herself standing uncomfortably in front of the guidance counselors office waiting for some sort of cue from the man inside that it's okay to come in.

He has his head down over his computer and his fingers move across the keyboard quicker than Jess can follow with her eyes.

She coughs lightly to signal her presence and is relieved when the counselor looks up. His beady grey eyes narrow at her but he beckons her in anyways. She sits nervously in the chair in front of him eyeing his nameplate which simply reads 'Marv' in elegant cursive.

"Am I in the right place?" She asks, glancing over her shoulder at the rest of the office area.

"Jessica Moore?" Marv prompts.

Jess nods, "Just Jess"

"That's not important," Marv replies with a wave of his hand as he flips through his file cabinet, 

"Ah, here we go. Your schedule," He says as he hands her the sheet of paper he's just picked out from the cabinet.

"Thanks I-"

"Someone will show you around likely Gabriel, Lord knows why, the only thing that moron can find is trouble." Marv interrupts, rolling his eyes, "Now if you don’t mind running along I'd like to get back to my novel sometime today."

"I- oh okay," Jess nods and quickly excuses herself from the office.

She’s moving so quickly out of the office that she very nearly barrels straight into a tall dark haired student just outside the office.

"Ah, sorry," She apologizes but if the other student hears her she is ignored.  
Okay so not a great start.

 

Jess is at her locker when Gabriel finally makes an appearance.

"Jess Moore?" He says, grinning impishly at her.

"Hi, uh Gabriel?" She guesses.

"Please," he replies, rolling his eyes, "Call me Gabe."

He's barely taller than her with sandy blonde hair and light brown eyes. She's only known him for all of one minute but there's something in the way he stands and the twist at the corners of his smile that reminds her of what Marv said earlier about Gabe finding trouble. He's exactly the kind of person she would expect to see goofing off in the middle of class or pulling pranks on unsuspecting classmates.

She realizes he's waiting on her response and nods quickly.

"Right so fortunately for you I get to show you around today." Gabe continues, starting off down the hallway.

Jess makes a grab for her things and quickly follows behind him.

"Now I know everyone and everything about this place so if you've got any questions just shoot." Gabe says.

"Yeah actually, the guidance counselor... is he always like that?" Jess asks, brushing a strand of long blond hair behind her ear.

"Marv!?"Gabe exclaims with a loud laugh, "Oh I love that dude! Total kook. Yeah he's always like that. Principals worse though. Real odd dude. I don’t think anyone's actually seen the guy in person to be honest."

"Oh," Jess says but she isn’t sure how that could be true unless maybe there was no shady principal and Gabe was just messing with her.

"Alright," Gabe interrupts her thoughts and waves a hand at a group of teens standing to one side of the courtyard, "Social rundown, let’s go. Those are the popular dicks. Don't worry about them though, those three on the left are my brothers so they won’t bother you.”

He motions to the back of the school where a few rougher looking kids smoke cigarettes and exchange angry sounding conversation; "That’s our local dangerous ruffian pack. Short version that’s Abby, Crowley, Lil, Al, and... damn, I never can remember that last one’s name but he’s got these really creepy urine colored eyes. Anyways If they try to talk to you, which they won't, don't look them in the eye and don't under any circumstances make any kind of bet with them."

He then points out a short redheaded girl sitting at an outdoor table with a skinny asian boy and an impossibly skinnier white boy, "Tech nerds," is all he says.

He waves to a group of well-dressed students sitting at the next table, "Rich kids," He scoffs, "Anna's alright and I actually used to date Kali, but Bela will dick you over if it means she comes out ahead and Gordon's just a dick."

Gabe makes like he's going to continue that train of thought but suddenly Jess is very distracted. She ignores Gabe’s next on the list of stereotypical high school cliques and instead watches as the most beautiful boy she's ever seen passes her by.

He's tall, a mop of shaggy brown hair falling into his eyes, and he has dimples when he smiles. 

He's walking with a dark-haired girl talking excitedly about something Jess is too far to hear. But she wishes more than anything in that moment that she could know what was making him so happy.

A pair of fingers snap her back to the present and Gabe’s face swoops in to block her view of the boy.

"Hellooo, anyone home? I'm not giving this lecture twice, so I hope you've been taking notes-"

"Who's that?" Jess interrupts

"Who's..." Gbe turns to follow her gaze and laughs when he sees who she’s looking at. "That?! Oh that’s Sam Winchester but trust me you don’t want to try it. His brother Dean's scary protective and everyone knows Winchester’s aren't allowed to date anyways."

"Who says?" Jess asks.

"John Winchester apparently, ex-marine, real tough looking dude too." Gabe says.

When he notices Jess's disappointment he adds, "Hey you don’t want Sam anyways. Guy's got pretty bad taste in company. You see that girl with him?"

Jess nods.

"That's Ruby. She used to be on the list of people you don’t screw with unless you want to spend your weekend in the hospital. And last year his best friend went crazy, had to be committed." Gbe informs her matter of factly.

"Still," Jess says, unable to help the tight feeling in her chest when Sam glances her direction.

She manages a small wave and Sam looks like he would wave back but the bell rings and a   
surge of students separates them, blocking Sam from view.

Maybe today isn't a total loss after all.

 

It's 2pm when Jess sees Sam again. She's standing making small talk with Gabe and his brothers, who have offered her a ride home. They're only waiting for the eldest brother, Michael to finish with his history exam.

Sam passes by them and Jess's heart does a spin. She waves nervously at him, completely forgetting her current conversation with Gabe.

"Looking good Winchester." Lucifer whistles from somewhere to her right.

Sam smiles at Jess, then rolls his eyes at Lucifer, but says nothing to either of them as he goes. 

Jess can’t help but feel slightly disappointed that Sam didn't rebuff Lucifer. But Gabe and Raphael seem to find Sam’s reaction hilarious.

"Lucifer, brother, you don't stand a chance with Sam Winchester. That boy is out of your reach." Raphael tells him.

"No one's out of my reach," Lucifer replies confidently, "Especially not Sam Winchester."

"Yeah?" Raphael says, raising an eyebrow, "Wanna bet?"

Lucifer shoots him a glance, "100 bucks say I seal the deal by prom."

"You've got yourself a bet" Raphael extends a hand and they shake on it enthusiastically.

"You’re both insane," Gabe says, "Dean will kill you."

Lucifer only laughs, "I'm not afraid of Dean Winchester."

Gabe shrugs, "Your funeral."

Jess nudges Gabe, "Hey uh, I'm going to go okay? But thanks for the ride offer."

She feels bad ducking out like this, but she has no interest in listening to Lucifer talk about his future relationship with Sam. Especially when she wants to be the one in the relationship with Sam.

 

Fate must be smiling on Jess today. She steps outside and sees Sam standing alone at the curb. She can’t let an opportunity like this pass her by, scary brother or not, so she approaches Sam and clears her throat.

Sam turns and he seems surprised until a flash of recognition crosses his face.

"Hi," Jess says, holding out her hand, "I’m Jessica, but my friends call me Jess."

"Sam," Sam replies with a smile, shaking her outstretched hand, "You're new here Jess?"

Jess nods, "Got any advice for the new kid?"

Sam laughs and it’s a beautiful sound, "Sure, uh let's see, you've probably already met Marv so I don't need to tell you to stay clear of him. I would also avoid Mr. Roman for economics, Mr. Cain for history, and the second-floor bathrooms."

"The second floor bathrooms?" Jss echoes.

"Senior bathrooms. They're known to be a little... messy at times."

"Ew," Jess wrinkles her nose in disgust which brings another light laugh out of Sam.

"Toughest subjects?" She asks.

"Ugh," Sam groans, "Depends on your strengths but Latin is my worst class by far."

Jess can hear what she’s about to say in her head and she knows it’s a terrible idea but her mouth is moving before she gets the chance to stop it. "Really? Do you need help? Because I know a thing or two about Latin."

Jess must be going crazy. That’s the only explanation for what she's just said because she knows all of two words in Latin and she's not even sure she knows those now.

"Seriously? That'd be great." Sam answers and he sounds so genuinely thrilled that Jess just offers a weak smile in return.

Fortunately, she’s saved by a sleek black car pulling up to the curb. Sitting in the driver’s seat is a senior boy she shares a study hall with. She doesn't know why she didn't notice before, but his light brown hair and playful smile is too like Sam's to ignore now.

"Sammy," The guy calls, "Quit flirting and get in, daylight's wasting."

"Dean." Sam hisses and his face is a deep red color.

"What?" Dean asks like he genuinely doesn't know what he's done.

"You're so embarrassing," Sam says, opening the passengers door and throwing his backpack in.

Sam slides into the front seat and pauses before shutting his door to say, "Thanks Jess, I'll see you around?"

"For sure," Jess says but Sam's door is already closed and the car is peeling out of the school parking lot.

Another car slides in to replace the black one at the curb. This car is bright red and clearly some sort of sports car.

From inside Gabriel waves to Jess and calls out the window; "still want that ride?"

Jess glances nervously to Michael in the front seat and he nods to her curtly.

"Thank you," She says as she climbs into the backseat next to Gabe, dictating to Michael her   
new address.

When the car starts moving again Gabe speaks up; "I saw you met Dean?"

Jess nods, "He didn't seem too bad."

"Did I say he was bad?" Gabe frowns, "Nah, Deans a good dude, pretty popular around here actually, he'd probably take over this high school if it weren't for his attitude. But it's just common knowledge you don't mess around with him or Sam."

"Oh," Jess says and suddenly her and Sam seem a bit more plausible in the long run.

Dangerously aggressive overprotective older brothers is something she would rather not deal with, but it doesn’t sound like Dean is that person. Or at least, Jess hopes he isn't.

Right now, she has more pressing problems.

Like learning Latin.

 

"Dean what is this?" Sam’s voice cuts through the classic rock playing in his headphones.

He blinks one eye open and squints at whatever Sam is holding.

"A piece of paper." He decides.

"Quit it Dean." Sam says, "This is an acceptance letter."

Dean shrugs, "So?"

"So, what's it doing stuffed in the kitchen drawer under my old Latin textbooks."

"Why were you looking for your Latin textbooks?" Dean asks, and damn, he'd thought that since Sam’s Latin was pretty close to perfect under the books was a great hiding spot.

"That's not... I told Jess I was struggling in Latin and she offered to help me out."

"Geez Sam!" Dean says grinning, "Smooth as chunky peanut butter."

"I don’t have to defend myself to you quit changing the subject. Why was your acceptance letter buried in the kitchen drawers?"

"Well officer if you must know it’s because I'm not sure I want to go."

"What? Dean you have to!" Sam exclaims.

"I don’t have to do anything," Dean shoots back, sitting up on the couch and pulling his headphones off his head, "Besides it's probably better if I stay close to home. It would be hell of a lot cheaper too."

"Dean-"

"Your turn, why'd you lie to Jess about Latin? You like her or something?"

Sam snorts which is practically an admission of guilt in Deans eyes.

"You totally do." Dean says.

"Yeah well too bad we can’t date." Sam replies shortly.

"I don’t know," Dean says, "Jess seems sweet. I’m sure dad would make an exception."

"Yeah right when has dad ever made an exception for anything." Sam replies, "I just don't get why he cares in the first place."

"Probably because of creeps like Lucifer." Dean points out.

"Lucifer's not too bad." Sam shrugs.

Dean lets out a humorless laugh, "And that's why were not allowed to date."

 

When Sam finally retreats back to his room to start on his homework, he leaves the acceptance letter open on the table.

There's a moment where Dean considers just leaving it but if he does that it might lead to further conversations like the one they just had.

So he stands up from the couch and takes the letter in both hands, running his eyes over the page before folding it quickly and stuffing it in his pocket.

He'd been surprised when the letter came. He'd applied on a whim and had fully expected and prepared himself for a rejection. So, he'd been completely caught off guard by an acceptance. He'd had no idea what to do with the damn thing thus the kitchen drawer and the stack of old textbooks.

He still has no idea what to do with it. All of his points he made with Sam are valid. School is an expense they can't afford, and his grades aren’t quite what they need to be for a scholarship. Besides, he really can’t leave Sam or their dad behind. What kind of brother, what kind of son abandons their family. Someone has to stick around and take care of things and that ship sailed for John the day their mom died.

Besides, Bobby's already told him he's willing to make Dean's summer job at the auto-shop a year-round gig should he decide to stay.

So there's stability in Lawrence. There’s family in Lawrence. And honestly does he need any more than that?

Dean takes the letter out of his pocket, gives it one last look, and drops it into the garbage can.

 

Jess meets Sam at the library on Tuesday. She’s read up on so much Latin that she’s seeing entire sentences on the backs of her eyelids when she shuts them.

The library is small but well stocked. It has a homey feel to it that makes Jess think she could get used to living here. Despite the various resources available Sam has brought with him a small mountain of textbooks. The pile is accompanied by various blank worksheets and Jess has to remind herself to be strong.

She thinks she does alright for the first two worksheets but by the time Sam reaches for the third she needs a break.

"So, she says," leaning back in her chair, "Have you always lived in Lawrence?"

Sam grins, "Yeah. My parents moved here when they got married."

"It's just you, Dean, and your parents then?" She asks.

Sam’s smile falters a little, "Um actually it’s just me, Dean, and dad."

"I’m sorry," Jess says quickly.

Sam shakes his head, "It's fine it happened when I was a baby."

"Still..." Jess desperately needs to change the subject before she says something else to upset him so without thinking she blurts, "So you really can’t date though?"

Sam gives her a surprised look and starts laughing. "That’s the rule," he says, thankfully not noticing how mortified Jess is right now, "But it's not a permanent thing. I’m sure if Dean started dating I could convince dad to let me too."

"Really?" Jess asks, her mind already racing, she needs to talk to Gabriel.

"Yeah but Dean isn’t really interested in that kind of thing so I'm pretty much doomed to be single till college." Sam explains.

Jess shrugs, "You never know," she says, "Maybe Dean will meet someone."

Sam snorts but doesn't say anything else. Instead he reaches for the third worksheet again and pulls out a pen.

 

"Let me get this straight." Gabe says, "Sam can date. But only if Dean does?"

Jess nods, her blond curls swaying in the early morning breeze. It's chilly today, even for February but none of the other students gathered outside in clumps before class seem to mind.

"Well that certainly makes things interesting." Gabe says and there's a glint of mischief in his eyes that Jess isn’t sure makes her nervous or excited.

"Interesting how?" She asks.

"The obvious thing to do would be to set Dean up with someone." Gabe tells her.

"Alright so we do that," Jess agrees.

"Hold on Amigo, that's so much easier said than done." Gabe shakes his head at her, "Dean... he’s not really the dating type. Sure, he flirts with just about everyone who breathes in his direction, but I don’t think he's had a real interest in anyone since Lisa Braeden in the fourth grade."

"Okay so what do we do?" Jess asks a little impatiently, wondering why he would suggest something only to shoot it down seconds later.

"We hire someone. That way they won't give up even if they’re initially rejected. The hard part is finding someone willing who's real personality is so bland we can mold them into being exactly what Dean wants."

"Where are we going to find someone like that. And isn't that pretty shady? Also, I have no money," Jess says and Gabe glares at her before continuing.

"See here's the thing. I've got this cousin, he's kind of a loner. The guys never had a real friend that wasn’t blood related in some way. Which makes him perfect for this. Not only will he be more likely to accept our social guidance, but we'd actually be doing him a favor with this. Dude needs to get out more." Gabe ends his explanation with a satisfied grin, like his plan is flawless.

But Jess immediately points out the one flaw she still sees, "That's great but that still leaves the money problem, I have none." Jess tells Gabe.

"And that’s where the real genius of it is." Gabe says and his eyes are flickering with mischief again, "We get Lucifer to back us on this."

"What? Lucifer? You get that the whole point of this is because I want to date Sam right?" Jess asks.

"Right, but so does he. We know about that bet with Raphael and trust me when I say Lucifer hates losing. So, if we pitch this to him right he'll pay for the whole thing and then we'll swoop in and reap the benefits."

Jess nods in approval, honestly she's impressed Gabe could come up with such a well thought out plan in such short notice.

"There, foolproof." Gabe says smugly, "Any more questions?"

"Yeah just one more thing. Your cousin. He's a guy, right?" Jess asks.

"Yeah." Gbe raises an eyebrow, "So?"

"It's just... is Dean gay?" Jess questions.

"Bisexual," Gbe replies, "Sam is too I think."

He gives her a long look as if daring her to have some sort of problem with this. When she doesn't say anything, Gabe seems pleased.

"Alright then!" He says, "Let’s get this plan into action."

 

The two of them approach Lucifer after first period.

In all honesty, the guy kind of scares Jess and she's glad to have Gabe by her side to confront him.

"Hey Lucy," Gabe greets cheerfully.

"Gabriel." Lucifer acknowledges, "What do you want?"

"Why do you assume I want something?" Gabe complains in mock offense.

Lucifer shoots him an impatient look and Gabe sighs raising his hands in defeat.

"You caught me I actually have a business proposal of sorts."

Lucifer snorts in disbelief, "You have a business proposal for me."

"Of sorts." Gabe says, "It'll help with you win Raph’s bet."

"I'm listening." Lucifer tells him.

"Ok so Sam told Jess here that he can't date until Dean does, right? So, here's the thing, if we can get someone to date Dean then you're free to take Sam to the prom."

Lucifer looks doubtful, but he nods at Gabe to continue.

"Well how bout we just pay Castiel to do it? Guy's never had a boyfriend in his life we could easily steer him in the right direction. It's a win-win situation. Our black sheep cousin becomes a little more normal and you get Sam."

"What do you get?" Lucifer asks smoothly.

"I can't just want to see my brother and cousin happy?" Gabe replies.

Lucifer snorts.

"Fine. I want the car for a week Drive around. Look fancy. You know the drill." Gabe relents.

Lucifer nods thoughtfully.

"Alright." He says, "You've got yourself a deal."

 

Castiel sits alone at lunch. He supposes this would make him easily approachable but then nobody's ever tried. So, when Lucifer comes up to him that day he starts wondering what he possibly could have done so wrong.

He's sitting where he always does so that can't the problem. He glances over at Lucifer’s table and no one is watching them or pulling out camera phones so this can’t be a dare of some sort. Well, someone is watching he notices, but its Gabriel and the new girl, Jess or something.

He's never been more confused in his life.

Lucifer takes the seat opposite of Castiel, sitting calmly and staring down Castiel as if he's trying to make him uncomfortable.

"Lucifer," Castiel acknowledges in hopes of breaking the silence.

"Castiel." Lucifer says calmly, his tone low and nonthreatening.

"Is there something you need?" Castiel asks.

Lucifer smiles and it's all teeth, "Now that you mention it, yeah, there is."

There's a brief pause where Castiel wonders if he should be saying anything. He opens his mouth to speak but Lucifer, either not noticing or not caring, continues over him.

"You see, I made this bet with Raphael. That I could get Sam Winchester to go to the prom with me. The only issue here is that Sam can't date until Dean does. You know Dean right? He's in our grade, brown hair, green eyes, about this tall," Lucifer raises a hand.

"I don’t see how this has anything to do with me." Castiel deadpans because he really doesn't, he isn’t particularly involved in the romantic lives of his cousins.

Also, this is the most Lucifer's spoken to him likely ever and for what reason? To tell him about his problems? No, Lucifer wants something he just hasn’t gotten to that yet.

"I want you to date Dean." Lucifer says.

Now its clear Castiel is supposed to break the silence but he doesn't even know where to start.

"That's... that's ridiculous. I don’t know anything about dating or Dean Winchester.”

Lucifer shrugs, “You’ll learn.”

“What? No. I won't do it." Castiel says, he can't believe Lucifer is even asking him to do this in the first place.

"Think about it Castiel I'll even pay you to do it. Besides it's not like you have to marry the guy. Just be normal for once in your life." Lucifer a snaps at him.

"I..." Castiel starts.

But the look Lucifer is giving him tells him that this is an order and it's not up for debate.

Lucifer pulls out two twenty dollar bills and slides them across the table.

Castiel reluctantly accepts them and glances at his older cousin.

"Good. I knew you'd come around," Lucifer says, "Now go over and sit with him."

"Now?" Castiel exclaims.

"No in two years, yes now." Lucifer rolls his eyes and gestures behind him.

Castiel follows his hand to the table in the far-right corner. He recognizes Dean instantly. He's sitting with the same group of friends he always does and laughing loudly at some joke the redheaded girl made.

Castiel knows he does not belong to that friend group and he has no business sitting with them and pretending. But Lucifer is eyeing him as if he's just waiting for him to disobey so Caestiel stands and gathers his lunch in his arms.

He almost stops and turns around three times on the way to Dean’s table but each time he does Lucifer is still watching him. So, he steels himself for rejection and walks straight up to the busy table.

"Excuse me, is this seat taken?" he asks, and his voice comes out a lot smaller than intended.

Fortunately for him all noise at the table has died down upon his arrival and four sets of eyes are on him.

He thinks he can name a few of the people at the table. There's Dean of course, and then the redhaired girl he thinks is called Charlie, the blonde girl is a junior and he doesn’t know her name, but the senior sitting on the opposite side of Dean from Castiel has to be Benny.

Finally after what feels like a humiliating eternity, the blonde girl nudges the redheaded girl and says, "Yeah man, seats empty, go ahead."

Charlie snaps back to action and nods her agreement.

"I'm Jo," The blonde girl introduces, "This is Charlie, Benny, and-"

"Dean," Castiel cuts her off, nodding and glancing at Dean next to him, "I know, I'm Castiel."

"Well not that it isn’t great to have you here Cas, but um... why are you here?" Dean asks.

Jo reaches across the table to smack Dean’s arm, "What Dean means to say is welcome."

"No, it's okay," Castiel surprisingly manages a laugh, he doesn’t know if he’s supposed to say anything about Lucifer but at this point he doesn't care.

He'd do anything to make this situation less awkward.

"My cousins think I should work on my people skills." He says with a nod to Lucifer's table.

They all turn to look very unsubtly at Lucifer who has been watching Castiel carefully and now waves to the table.

Castiel doesn't think the others notice the way Lucifer’s eyes burn with anger even from across the lunchroom and he decides it's probably best not to mention Lucifer again.

The group seem to accept this explanation without further questioning and lunch proceeds as if Castiel weren't even there.

As does lunch the next day and the next after that.

It’s not until Friday afternoon of the next week that Castiel actually starts making progress despite Lucifer’s constant pressure to make his move. Castiel’s people skills might be rusty that’s true, but it would be silly not to mention horribly embarrassing for him to make a move so soon. Unfortunately, Lucifer doesn’t seem to understand that patience is a virtue. Lucifer has set his sights entirely on Sam and right now he only sees Castiel as a means to an end that he cannot wait for.

So Castiel not only has to work on getting closer to Dean, he also has to stave off his mildly terrifying cousin who’s never had to wait for anything in his life and therefore can’t seem to comprehend that building relationships take time.

Not that Castiel is having any success with this anyways. He’s eaten lunch with Dean for the past week and only said maybe three full sentences to him. He tells himself(and Lucifer) he’s observing Dean and his friends, gaining information. But truthfully, he has no idea how to make   
Dean fall in love with him.

Fortunately or unfortunately, it soon becomes clear that Lucifer is not the only cousin with an interest in this disaster. Gabriel approaches him after Fridays quiet lunch period, Jess in tow.

“Hiya Cuz’,” He greets, “This is Jess.”

“Gabriel what do you want.” Castiel doesn’t bother with hello’s, he’s already dealing with one cousins impossible request and he’s not eager for another.

“Wow, touchy.” Gabe says, raising his hands, “I don’t want anything.”

Castiel narrows his eyes, unbelieving.

“We want to help you.” Gabe clarifies.

“Sure.” Castiel says, stepping around Gabriel and towards his locker.

“I mean it Cas,” Gabe blocks his movements, “Think about it Cas, does Lucifer seem smart enough to have come up with this plan? No, right? Because it wasn’t his plan.”

Castiel stops moving at this and Gabe continues talking seemingly unaware that Castiel is now glaring in silent anger at him.

“It was my plan. See Jess here is the one who really wants to date Sam, Lucifer is just our pawn. We convinced him to pay you, you’re welcome by the way, to date Dean. But pretty much everyone watching can see you struggling so Jess and I are here to help you out. Consider us your Dean relationship fairy godmothers.”

He ends his statement proudly and looks to Castiel like he’s actually expecting a thank you for this.

“Let me get this straight.” Castiel begins, keeping his voice deceptively calm, “I have to either find a way to date Dean Winchester or leave the country to avoid Lucifer’s unending wrath because of you?”

“Ah. Don’t be mad,” Gabe says, his confidence faltering.

“Mad? I’m not mad. I’m furious.” Castiel laughs, “How could you do this to me?”

“Oh come on Cas, don’t be so dramatic. It can’t be that bad can it? Dean’s pretty cute don’t lie.”

“I don’t- It’s not- that’s not-“ Castiel wants to strangle the knowing look off of Gabriel’s face.

Yes, Dean is cute, not that Cas would admit that out loud and especially not to Gabriel who got him into this mess to begin with. Were the circumstances different then yes Castiel might have been interested in a relationship with Dean. But the circumstances are not different and he’s only trying to date Dean out of fear for his cousin which doesn’t seem like a decent way to build an actual relationship at all.

“Whatever,” Gabe says but he’s still got a grin on his face the implication of which Castiel hates, “Either way, you’re struggling. You need our help.”

“I don’t want your help.” Castiel tells him.

“I didn’t say you wanted it.” Gabe shrugs, “But unless you want your ass kicked six ways to Sunday by Lucifer when he doesn’t get Sam or the 100 bucks he bet Raphael I suggest you take it.”

Castiel is still furious, but he sighs and gives in, “Fine, what did you have in mind.”

It’s Jess who speaks next, “Sam says there’s a music store downtown Dean likes to spend time at, and he’s pretty sure Dean will be there this Saturday for the latest albums.”

“So?” Castiel asks.

“So, go there!” Gabe says like it’s obvious, “Act like you’re interested in classic rock or jazz or whatever lame music he enjoys.”

“But I’m not interested in jazz,” Castiel replies, confused.

“It’s an example Cas, and it’s not important anyways, just pretend you’re interested.” Gabe rolls his eyes.

Castiel must still look dubious even though he’s already decided to go (what choice does he have, Lucifer is growing ever impatient waiting for results) because Gabe adds, “Look, I have the mustang this weekend, I’ll let you borrow it.”

Castiel knows the mustang is Lucifer’s car and if anything were to happen to it under Gabriel’s watch…

“Fine, drop the car off at 1. I’ll do it.” Castiel agrees and the two juniors in front of him sigh in relief.

“Great!” Gabe says, “See you around Cuz’.”

Castiel shakes his head as they pass him on their way to their next class. He still can’t believe Gabriels’s managed to drag him into this mess and he doubts this will end the way anyone wants it to.

His hand brushes his wallet inside his backpack as he reaches for his textbooks and he thinks of the 40 dollars Lucifer slid him nearly two week ago still folded nicely in the front pocket of the wallet.

Maybe he’ll buy himself something nice this weekend.

 

True to his word Gabriel rolls into Castiels driveway in the Ferrari at 1pm sharp. He passes the keys to Castiel with extreme reluctance.

“Look man, I know you’re pissed but please don’t do anything I’ll regret.” Gabe begs.  
Castiel just shrugs and gets into the car, turning the keys and feeling the engine come to life.

“I’ll be careful,” He says with no real conviction.

“Cas-“ Gabe begins, but Castiel is already driving away, following directions given to him by Jess who got them from Sam.

They would be confusing to someone not from Lawrence but Castiel has lived here long enough that it’s not a problem.

He finds the music store without trouble, the sign reads ‘Turner Records’ in large red lettering. Castiel immediately recognizes the shiny black ’67 impala parked just outside the store. He parks his own car around the block and plans his run-in.

It has to be casual, like Castiel hadn’t driven here with the sole intent of meeting Dean. Maybe he walks into the store and starts looking for music? But Castiel doesn’t listen to much music and if Dean really does come here often would he notice that?

Castiel finally works up the nerve to get out of the car and walks towards the music store. He’s two feet from the entrance, one foot, he’s there, and then he keeps walking, not even attempting to grab the handle of the door. What was he thinking, he can’t do this, there’s no way. It was one thing when he was in the cafeteria sitting with Dean and all of his friends, but this is something else entirely. He’s going to have to talk to Dean, look him in the eye probably. And instantly this all seems overwhelming. What was he thinking agreeing to this. What was Lucifer thinking asking him to do this? What was Gabriel thinking suggesting this to Lucifer? He walks past the store again this time in the direction of the car.

He gets halfway down the block before he turns around and heads back to the store. He can do this. It’s just talking nothing even has to happen now he just has to say hello to Dean and then he can leave. Besides, Lucifer will destroy Castiel if he doesn’t start getting results soon.

He makes it to the door this time, grips the handle, then walks away.

No, he can’t do this. He walks three steps, turns back, grips the door handle again with renewed confidence and can’t bring himself to pull.

Castiel sighs. He’s going to be doing this all day at this rate. He can’t go inside but he can’t bring himself to leave either. He briefly considers waiting outside for Dean to come out but that could be creepy, so he turns back to the car and fights the feeling inside that tells him to turn around again. Behind him the door swings open and the bell above the door rings as whoever it is leaves.

“Hey! Cas!” A surprised voice calls out.

It’s Dean.

Castiel turns slowly, “Hello Dean,” he says and he honestly believes he must have the worst luck for this to happen right as he was ready to leave.

“Wow, didn’t really think I’d run into you here,” Dean says, glancing back at the store behind him.

“It’s Gabe’s birthday.” Castiel lies smoothly, “I uh needed to find him a present.”

“Really? I thought Gabe’s birthday was in March,” Dean muses, “What did you get him?”

“I um, I got him-“ Castiel finds himself struggling to come up with a second lie especially when his first was discovered so easily.

Luckily he’s saved by Lucifer passing them in Michael’s deep blue Porsche.

“Hey Winchester,” He calls, “Where’s your brother?”

“Shove it Lucifer!” Dean shouts, raising the finger at him.

“Yeah? Just tell me where you want it Dean,” Lucifer calls back and Dean scowls, unable to form a come-back before Lucifer drives off.

“I hate that guy.” He growls, then quickly looks to Castiel sheepishly, “Er, no offense.”

Castiel shrugs, “None taken, it’s likely that I hate him more than you do.”

“Not possible,” Dean shakes his head with a smile.

“Why is he so interested in Sam?” Castiel asks.

“Your guess is as good as mine.” Dean says, “Guys a creep, he’s probably just bored or maybe he gets off on the challenge.”

“That hardly seems like a reason to pursue someone,” Castiel replies and he’s fully aware of the irony in him judging others reasons for romantic interest.

“No kidding.” Dean nods.

Dean looks around, bringing a hand to shade his bright green eyes from the sun. Castiel takes notice of a dusting of freckles across Dean’s nose and cheeks. He really is, as Gabriel put it, pretty cute.

“Where are you parked?” Dean asks, “Don’t tell me that rust bucket across the streets yours?”

Castiel shakes his head, “I’m parked up the block.”

“Good,” Dean says, “I don’t think we could be friends anymore if that were your car.”

Dean doesn’t seem to notice but Castiel feels a burst of happiness at the implication of the word ‘anymore’.

“Actually,” Castiel begins, an idea forming in his head, “You should come see my car,”

Dean glances at his impala, then down the block and shrugs, “Sure.”

Castiel leads the way down the block and around the corner, coming to a stop in front of Lucifer’s cherry red mustang convertible.

Dean’s eyes widen and he whistles low as he approaches the car, placing a hand on its side door. “That’s a nice car Cas.” He says.

Castiel grins, “It’s not mine.”

“No?” Dean doesn’t look up from where his eyes are running over the dashboard.

“It’s Lucifer’s.”

Deans head jerks up to look at him and there’s a sudden wild excited look in his bright green eyes, “Is it now?”

Castiel nods and tosses him the keys, which Dean catches in one hand.

“Shall we?” Cas asks.

Dean tilts his head towards the car and slides into the driver’s seat, “Only if you insist.”

Castiel laughs and gets in on the passenger’s side.

Dean has the keys in the ignition and is about to start up the car when he hesitates.

“Wait, won’t Lucifer kill you for this?” Dean asks, raising a brow.

“Gabe’s supposed to have the car for the weekend.” Castiel assures him.

“All of the fun none of the blame. Can’t argue with that.” Dean says and Castiel smiles.

“No you cannot.”

 

Dean has to admit, he’d been on the fence about Castiel, the guy was kind of a loner. When he’d first sat down with them at lunch Dean had expected there to be a catch or a reason. He was related to Lucifer after all, outcast or not.

But as the two of them tear down the highway in Lucifer’s car, the wind ripping through their hair and blowing bits of their conversations back down the empty road, Dean decides he must be cool if he’s enjoying this as much as Dean is.

Castiel is laughing at something Dean has said and he has one hand dangling outside of the car. He has a nice laugh and Dean thinks he could get used to listening to it if Cas sticks around.

“Hey, where are we going?” Cas shouts to him over the combined noise of the engine and the wind.

But he doesn’t sound concerned with the destination as much as thrilled by the journey.

“Ever heard of The Roadhouse?” Dean calls.

“No!” Cas exclaims happily, “I’ve never been outside of Lawrence.”

“Seriously?!” Dean asks.

Cas nods, “Guess I’ve never really had good reason to.”

“Huh.” Dean says but he’s pretty sure it’s lost to the wind so he raises his voice for the next part, “Well you’ll love The Roadhouse. Jo’s mom runs it. It’s about 10 miles outside of town.

“Jo the junior Jo?” Cas asks.

“No the Jonas brother.” Dean mocks, “Yes Jo the junior.”

Cas laughs again, throwing his head back as he does. Dean watches the way his whole face lights up when he does. It almost convinces Dean that what he said was actually secretly hilarious.

His stomach does a flip and he tears his eyes away to focus back on the road ahead.

“So what’s your beef with Lucifer?” He asks Cas.

Cas shrugs, face becoming serious, “I’m sure you’ve gathered he’s not the kindest or the most respectful person. But he treats his family members as if he is our leader. We’re supposed to do as he asks without question. Michael’s really the only one keeping him in check.”

“And Gabriel?” Dean asks.

Cas frowns, “I don’t dislike Gabriel.”

“Well you don’t risk Lucifer’s wrath on someone you love” Dean snorts and Cas can’t argue with that.

“Gabriel, he thinks he knows what’s best for me and I truly believe he is trying to help me, but his methods leave much to be desired,” Cas says, laughing to himself at a joke Dean doesn’t understand yet, “But this isn’t- I don’t hate Gabriel, this is just revenge for a specific occurrence.”

“Hell of a revenge.” Dean says.

"Believe me," Castiel says seriously, "He's getting off easy."

"Geez what did that poor sucker do?" Dean asks

Cas opens his mouth to answer but The Roadhouse is in sight now.

"Hold that thought, Cas," Dean holds up a hand as he steers the mustang into the parking lot, carefully backing into a spot between two trucks.

Both trucks have clearly seen better days and the mechanic in Dean desperately wants to direct their owners to Singer's Autoshop.

He turns off the mustang and pockets the keys without thinking. If Castiel notices this however, he says nothing and follows Dean quietly into The Roadhouse.

Jo is at her usual place behind the busy bar, sliding drinks to already red-faced customers.

Cas leans in to Dean to whisper, "Is that legal?"

Dean turns and whispers back, "Snitches get stitches Cas."

Cas snickers but says nothing more on the subject.

Jo spots them and her face lights up, she waves Dean over enthusiastically and passes him a beer.

"Want anything?" She asks Cas.

"That's definitely not legal." Cas replies, glancing from Dean to Jo.

Jo laughs loud and enthusiastic.

"I won't tell if you don't," She says.

Dean shakes his head, grinning at his childhood friend.

"One of us has to drive back." Dean tells Jo and she pouts.

"Too bad," She says, "I get the feeling Cas here is a fun drunk."  
Dean laughs into his cup at the thought of Cas being drunk. Cas is generally so quiet and serious he can't even picture him any other way.

"That better not be a beer in your hand Dean Winchester." A voice interrupts from behind them and both Dean and Cas turn in their chairs.

"Hey Ellen," Dean greets smoothly, "Of course not you know I don’t drink."

"Uh-huh" Ellen nods, clearly not falling for the lie. "Then you won’t mind if I try it hm?"

Dean sighs, knowing he's caught and hands what's left of the beer to Ellen.

"Joanna Beth you keep the alcohol for paying customers." And before Dean can reach for the five dollars he has tucked in his jeans picket she clarifies, "Legal paying customers."

"You're no fun Ellen." Dean gripes.

"And you're not 21." Ellen replies, ruffling a hand through Dean’s hair.

"Who's this," She asks, nodding towards Castiel.

"That's Cas, mom," Jo answers, sliding a coke to Dean with a sympathetic, "Better luck next time."

"Nice to meet you Cas I'm Ellen," Ellen says, holding out a hand which Cas accepts and shakes.

"Good grip, I like this one," Ellen decides.

"Thank you Ma'am," Cas says and Ellen lets out a burst of laughter incredibly similar to her daughters.

"I definitely like you," She says.

 

A few moments later Ellen is called away to deal with a handful of rowdy patrons and Jo is tied up taking orders and it's just Dean and Cas again.

Except this time Cas is asking the questions.

He asks about Deans classes, Deans friends, Deans brother, and by the time Dean is done ranting about Sam and how proud he is of his genius kid brother, it's three full hours and a burger meal later than when they arrived.

“Hey do you need to get back?” Dean asks finally, “You know, with the car?”

It might be just his imagination but Dean thinks for a moment he sees a flicker of disappointment on Cas’s face.

“Probably,” Cas replies.

Dean nods and stands, calling out a goodbye to Ellen and Jo.

Cas pulls out his money to pay for the meal but Ellen calls from the back, “Don't you think of it Mister. Meals on us, welcome to the family” and Cas practically glows at that.

Dean pulls the keys from his back pocket, and settles his to-go cup of soda into the cupholder.  
It's barely 5pm but the sun has already dropped from view giving way to a large half-moon and a sky full of stars. Cas seems content to stare up at them on the ride back and Dean finds himself surprisingly comfortable in the silence. The wind whipping around them is significantly cooler now than it was this afternoon but neither of them seem to mind.

They're about two minutes from town when Castiel finally speaks.

“I’m sorry.” he says.

“For what?” Dean asks.

“For Lucifer. And this whole thing with Sam.”

Dean snorts, “Like that's your fault.”

Cas sighs and rests his hand on his cheek, gazing off into the distance, “He's my cousin,” Is all he says.

“Doesn't make you responsible for what he does.” Dean says, “Besides, there's nothing to apologize for. I'm going to make sure of that.”

“Sam is very lucky to have you,” Cas tells him.

“Try telling him that,” Dean replies, “Little snot can't wait for me to go off to college.”

“I'm sure that's not entirely true.”

“True enough.” Dean sighs, “He found my acceptance letter last week and hasn't dropped it since.”

“You don't want to go to college?” Cas asks and for a moment Dean is surprised.

Truthfully he doesn't know what he wants and he can't remember the last time someone asked him about it.

“Someone has to take care of Sam and dad.” He reasons.

“Why does it have to be you?” Cas asks softly.

“Who else would it be?” Dean replies, letting his hand dangle over the side of the car.

Cas is quiet at that and they pull into the music store parking lot next to Dean’s impala.  
Dean gets out of the car and moves to the impala. He's about to get in when he hesitates.

“Hey Cas?” He calls, his voice seeming to echo around the now emptied streets.

“Yes Dean?” Cas answers.

“You're welcome to keep sitting with us. At lunch I mean. If you want to.” Dean says.  
Cas pauses for a brief moment and Dean is scared for a solid two seconds that he'll say no.

“I'd like that.” Comes Cas’s reply.

“Oh.” Dean says, “Okay. Great. Well I'll uh, see you ‘round then. Goodnight Cas.”

“Goodnight Dean.”

 

Castiel watches the impala’s tail lights disappear from view before sliding into the driver's seat of the mustang.

Dean has left his soda behind, he notes.

Cas’s hands grip the steering wheel where Deans were less than an hour ago.

He should feel something. Guilt. Embarrassment. Anxiety.

But he just feels happy.

He glances at the soda Dean left behind.

He shouldn't be feeling happy. None of this is real. This is just something he's been tasked with by Lucifer and Gabriel. It would be cruel of him to make it into something else.

Dean has left his soda behind.

Castiel removes the lid and pours it onto Lucifer’s pristine leather passenger seat.

He drives home satisfied.


	2. Chapter 2

**Summary for the Chapter:**

> Featuring more direct quotes from the movie and also my favorite party scene of any teen flic.

Dean arrives home to find Sam at the kitchen table working math problems from his textbook and John Winchester passed out on the living room sofa, tv still blaring some trashy reality show.

Sam glances up when he enters the room and gives him a nod before going back to his work. Dean slides the remote from Jahns hand and powers off the tv. He drapes a blanket over his snoring father and takes the empty beer bottle from the floor to the kitchen. 

“Hey Sammy, how’s it going?” He asks, falling into the chair next to Sam at the dining table.

“Good.” Sam says shortly and Dean can tell it’s going to be one of those conversations before Sam even opens his mouth the second time.

“I’ve been thinking.” Sam puts down his pencil and turns to Dean.

“Uh-oh,” Dean says.

Sam ignores him and continues, “I think you should go. To college I mean.”

“We’ve already had this conversation Sam aren’t you getting bored of no?” Dean sighs.

“I just think… I think it’s what mom would have wanted,” Sam says softly, and he doesn’t mean to start anything by it but the mention of their mother strikes a chord in Dean.

“What do you know about what mom would have wanted,” Dean snaps at him.

"I-" Sam starts.

"No. Don't give me that bullshit you don’t know anything about what mom would have wanted. You didn't even know her." Dean says angrily.

"I guess not." Sam replies and now Sam is furious.

He stands abruptly, slamming his textbook shut and throwing down his pencil. He shoves his chair into the dining room table so hard it tips over and storms towards his room.

"Sam, come on I didn't mean it like that." Dean tries, instantly filled with regret.

"Yeah then how did you mean it, Dean?" Sam shouts, glaring from where he stands in his doorframe.

"I…" but he doesn't have a good answer.

"That's what I thought." Sam says and he slams his door behind him.

 

“Gordon Walker. I can’t stand that guy. Pompous, arrogant, dou-”

“You’re just angry Kali left you for him.” Jess interrupts Gabriel’s rant.

“Not true, jerk’s been a pain in my backside since kindergarten when he stole my favorite set of crayons.” Gabe huffs, picking at his lunch in annoyance.

“Your favorite set of crayons! What are you going to do?” Jass gasps, twirling her own fork around in her spaghetti.

“Sarcasm not appreciated.” Gabe tells her, “Anyways, I still owe him payback for mocking me in english last week.”

“I take it you have something in mind?”

“Even better, I already have something in action.”

“Share with the class?” Jess asks, sitting forward at her seat.

“You know about Gordon’s party this Friday?”

“No?”

“Exactly.”

“Okay…? So?”

“So I printed up flyers for it.” Gabe says smugly.

“For his nonexistent party?” Jess asks slowly, not quite catching on yet.

“Sweet summer child, it exists, only Gordon doesn’t know it yet.”

Jess finally gets it, “Okay. Wow. Will that even work?”

“It better, I spent 12 dollars printing all these flyers.” Gabe laughs, “Anyways I was thinking this would be a great opportunity to invite Sam out.”

“You think?”

“Of course! Highschool party, lots of alcohol, lack of parents. It’s perfect.”

“But what about Dean? Sam can’t go it Dean doesn’t.”

Gabe winks at her and nods his head behind them. Jess turns to glance over her shoulder at Dean’s table where she finds he is sitting awfully close to Castiel.

“Somehow,” Gabe says, “I don’t think that will be a problem.”

 

Gabriel is still fuming over what Castiel did to Lucifer’s car but he walks up to him Thursday afternoon after class anyways so Castiel figures it must be important.

“I need you to take Dean to Gordon Walkers party this Friday.” Gabe says, not wasting any time.

Castiel frowns, “Gordon’s not having a party.”

“He will be.” Gabe says, “Trust me this Friday, it’s practically a done deal.”

Castiel is still skeptical, “I don’t like parties, Gabriel.”

“It’s one night Cas. Besides you owe me. I covered for you for what you did to Lucifer’s car man. Soda in the front seat was not a fun explanation to give.” Gabe says.

“You deserved that.” Castiel tells him adamantly.

“No one deserves that.” Gabe replies.

Castiel considers this. He does have no other plans for Friday anyways and Lucifer had slipped him an extra 20 that morning telling him to ‘keep up the good work’. Not that he needed or really wanted Lucifer’s money to convince him. Truthfully, he’d known he would agree as soon as Gabe suggested he take Dean anywhere. It was stupid, but he was actually kind of grateful for an excuse to see Dean outside of the lunchroom. And the thought of going to Gordon’s yet to be announced party together sounds fun.

“Look, if you’re worried it’s not going to happen it’s going to happen, I’m going to spread the news tomorrow afternoon. It’s going to be great.” Gabe smirks, “I can already see the look on Gordon’s stupid face when people start showing up at his house.”

“Gordon doesn’t know about the party?” Castiel asks, then noticing the look in his cousin’s eye waves a hand, “Nevermind I don’t want to know.”

Gabe laughs, “Smart. See you Friday then?”

Castiel sighs, hoping this won’t be a mistake, “Yes.”

“Great! No take backs. Jess kind of already invited Sam.” Gabe says and before Castiel can even consider replying Gabe is gone.

Castiel wonders what Gabe is really getting out of all this. Originally he’d assumed it was Lucifer’s car for a week. Now however, he’s almost certain Gabe is just enjoying the sheer chaos all this is surely going to cause. Because things seem to be going smoothly now but Castiel knows it won’t last forever. If Jess starts dating Sam, Lucifer will throw a fit and who knows what could happen then.

‘He could tell Dean’ Castiel thinks and a wave of panic hits him

He shouldn’t be so afraid of this outcome. Dean will likely find out what’s going on even if Lucifer gets Sam. Then Dean will hate him. And it will be what he deserves.

But for now at least, Dean doesn’t hate him and Castiel thinks he might actually like spending time with Dean so he shuts his locker, and sets off to find him, swinging his backpack over his shoulder.

He hears Dean before he sees him.

Dean is standing in the nearly empty science wing but he’s not alone. Sam is with him and Dean is trying to keep his voice low as the two of them argue.

Castiel hangs back around the corner but doesn't leave. 

“This isn’t still about Saturday is it? Look I said I was sorry can we just move past it?” Dean is saying.

“Yeah, we’re past it.” Sam replies in a tone that implies he is clearly not past it.

“Good then- that’s good.” Dean says.

“Good.” Sam says shortly, “So I can go to the party then?”

“Sam,” Dean starts, and he sounds tired, “I don’t think it’s a good idea. I wasn’t really planning on going.”

“So? I can go without you I don’t need you watching me all the time I’m not a baby.” Sam snaps.

“No I know you're not a baby. Just, Lucifer’s going to be there. And likely Gabriel and I don't trust either of them when they are sober and supervised.”

“I'm going with Jess not Lucifer. Can you at least pretend to trust me not to do anything stupid?”

“I trust you.” Dean tries.

“No. You don't.” 

And then there are footsteps headed towards Castiel. He has the vague thought that he should probably act as if he weren't just listening in on their entire argument. But then Sam rounds the corner into the hallway Castiel is in. 

Surprise to see Cas breaks through the anger on Sam’s face for barely a moment.

Then Sam is pushing past him and calling over his shoulder, “Your boyfriend was eavesdropping by the way.”

“I wasn't-” Castiel protests at the same time Dean comes around the corner and says “He's not my-”

But Sam isn't listening to either of them.

Castiel is pretty sure his cheeks are the color if Lucifers car by now but he turns to face Dean anyways. 

Dean rubs his forehead with one hand and lets out a heavy sigh. 

“Hey Cas.” He greets, “Now's not a really great time.”

“I understand, I'll leave you alone.” Castiel says, backing away slowly. 

“No that's not- nevermind, it's fine. I just don't understand him sometimes.” Dean stops him.

“That's probably for the best.” Castiel muses, “After all, he doesn't seem to hate Lucifer.”

Dean huffs out a stiff laugh, “True but that's not what I mean.”

Castiel tilts his head in confusion.

“I'm just trying to protect him.” Dean says, “Why can't he see that?” 

“Protect him from what?” Castiel asks.

“I don't know. Lucifer? Teenage pregnancy? The whole damn world?”

“Somehow I don't think you should worry about Sam becoming pregnant.” Cas assures him and Dean’s laugh is slightly less forced this time.

“And Sam,” Cas continues, “He's smart. He would never intentionally endanger himself.” 

Dean nods, “It's the unintentional stuff I’m worried about.” 

Castiel nods his agreement and there's a moment of comfortable silence between them before Dean speaks up again.

“This thing Friday,” He says, “The party that everyone seems to know about but me. Are you going?”

“I thought I might.” Castiel tells him and this is it, here is the perfect opportunity to ask Dean to come with him.

But before he can open his mouth to form the question Dean blurts, “You shouldn't go alone you know.”

Cas smiles, “Of course not. Would you like to come with me Dean?”

Dean returns the smile, “I'll have to check my calendar but I think I'm free.”

“That's great news.” Castiel says.

And he honestly means it.

 

Sam is waiting for Dean at the impala, his hands shoved deep into his pockets and a scowl on his face.

“What took you so long.” He asks Dean as he unlocks the doors for Sam and slides into the driver's seat.

“Would you believe I was chased down by a pack of rabid dogs?” Dean responds. 

“No.” Sam says. 

“Too bad.” Dean says, “They were vicious. I only just lost them.”

“You're hilarious.”

“I like to think so.”

Dean starts up the impala but doesn't make any moves to take her out of park.

“Sam.” He says.

“Dean.” Sam says.

There's a period of silence where Dean thinks about what he's about to say.

“You should go to the party with Jess.” Dean tells him finally. 

“Really?” Sam’s eyes widen and a smile starts to form on his face.

“Yes really, you're right you're not a kid anymore. And I can't stop you from going.” Dean says.

He pulls the impala out of park and backs out of the parking lot.

“What's the catch?” Sam asks.

“I drive and you're home before 12.” Dean says.

“Ruby drives and I'm home before 11.” Sam counters. 

“Fine.”

“Fine.”

“Does that mean you're going too?” Sam asks.

“I might swing by.” Dean answers. 

“You're going with Cas aren't you?” Sam guesses. 

“He might be there.” Dean replies.

“I knew it. He's good for you Dean.” Sam nudges Deans side with his elbow,”He's pretty too.”

“Bitch” Dean says with no real fire behind it.

“Jerk.” Sam replies with the same lack of heat.

And for the first time since Saturday there's peace between them.

 

Cas offers Dean a ride Friday and to be honest Dean is grateful. This isn't his first party, he knows that sometimes property gets damaged, and he definitely doesn't want to be repairing broken windows or cleaning puke off the hood of his Baby the day after.

But when he sees Cas’s run-down ford he briefly considers walking.

“No mustang today?” He jokes. 

Cas shrugs,”We can’t all have money.”

“I guess not.” Dean says, “Are you sure that thing runs?”

“I drove it here didn't I?” Cas retorts. 

“If you say so.” Dean locks the front door to the house behind him and walks up to the car, running a hand over the hood.

“On the bright side we won't have to worry about getting back. No one's going to hotwire this car.” He muses.

Cas rolls his eyes and glances to the front door, “Does Sam need a ride too? I'm assuming he has been allowed to attend.”

“Nah,” Dean assures him, “Sam’s riding with Ruby.”

“Excellent.” Cas says, getting into the driver's seat and starting up the car which makes an awful rattling noise as the engine turns. 

“That doesn’t sound too good Cas.” Dean frowns, “When was the last time you had this thing checked out?”

And Castiel looks like he is thinking way too hard on an answer that should be simple.

“Too long,” He says finally.

“You know I could take a look at it for you sometime,” Dean offers.

“You know about cars?” Cas raises an eyebrow.

“Only as well as I know my name.” Dean says, and he sounds a little offended that Cas even asked, “I work over at Bobby Singer’s in the summer. If you bring this thing over there and convince Bobby it's not junk I'll fix it up for   
you.”

“I would very much appreciate that, Dean,” Cas says.

And it's weird how natural this feels. Like they've been friends for years not weeks. It would make Dean nervous if he thought he had anything to be scared of in Cas.

He almost wants to say something about it. Ask if Cas is feeling this too. 

“Don't mention it,” is what he says instead and the rest of the short ride is spent in silence. 

Silence which makes it impossible to miss the ongoing party. 

They can hear the damn thing from blocks away and it's a wonder the cops haven't been called yet. The music alone is thirty times louder than anything either of them has ever heard. Then there's the people, shouting to the music, shouting to each other, shouting in general.

“Wow.” Cas says and Dean glances over to find him gripping the steering wheel so tight his knuckles turn white. 

“You okay?” Dean asks. 

“It's very loud,” Is all Castiel says.

“Do you want to leave?” Dean tries again.

Cas looks at him and blinks a few times as if to clear his head.

“No,” he decides, “We're here we might as well go in.”

“My man!” Dean exclaims, clapping Cas on the back before hopping out of the car and making his way towards the house.

Cas follows closely behind as if he's worried he'll lose Dean in all the commotion but Dean makes sure to keep Cas in his peripheral.

It's pretty obvious the dude has never been to a party before or at least not one this large scale and he doesnt fit in. It's not entirely surprising though, after all Cas did have the reputation of being kind of a loner. So Dean decides he'll try his best not lose Cas in the crowd. Not that he was planning on it anyways.

The speakers are blaring some Alanis Morissette song about rain on your wedding day and Dean scans the room for Sam. It's likely his brother is already here hopefully with Jess and not Lucifer. 

He spots Gordon in a corner fuming with anger and Bela next to him trying to get him to calm down. Gabriel is dancing in the center of the room, spilling whatever is being passed around in the thick red solo cups all over the floor. He even thinks he sees Charlie with her girlfriend walking towards the kitchen and he moves to catch up with her. 

In his haste he doesn't realize Cas is no longer with him and when he turns to go back for him he's cut off by Lucifer. 

“Looking hot Dean.” He sneers, “Of course, not as hot as Sam is tonight.”

“Say that again.” Dean dares him but Lucifer is already walking away laughing loudly. 

And damn, if Dean wasn’t already convinced that he needed to find Sam first that interaction would have done it. So he momentarily forgets Cas and reaches for a drink as he starts his sweep of the house. 

 

He finds Sam standing awkwardly with Jess at the base of the stairs.

“Hey, Can I talk to you for a sec?” Dean asks Sam.

Sam glances from the cup in Deans hand, which is now holding his second drink, to Jess who shifts uncomfortably, “Sure.”

“Just thought I should warn you, Lucifer’s being extra douchey with a capital D tonight.” Dean says loudly to be heard over the music.

“Okay.” Sam doesn't seem to understand why Dean is telling him this even though this feels to Dean like the most important piece of information he's ever needed to give. 

“You should probably steer clear of him.” Dean tries again.

“Seriously Dean?” Sam asks and he seems annoyed although Dean can't comprehend why, “Give it a rest. I thought you over this. I'll be with whoever I want. And didn't you come here with Cas?”

Cas, right. Where was Cas?

“Go find him and leave me alone,” Sam finishes and he looks up and smiles at someone across the room.

“Hey!” He calls with a pointed look at Dean, “Lucifer, wait up!”

“Sammy!” Dean makes a grab for his brother but Sam wrenches out of his grip and keeps walking.

“Hey don't-” Dean starts angrily but Sam whirls on him before he can finish his sentence. 

“Cut it out Dean. I'm not a child anymore.” He snaps, then adds, “You're embarrassing yourself,” before turning and catching up to Lucifer.

Lucifer wraps an arm around Sam and slides his hand down Sams back, sending a gloating suggestive look in Deans direction

Dean finishes his drink

 

Castiel is lost.

He knows that. 

He doesn't know where Dean is or where Gabe is or even what room of the house he's in but at least he doesn't pretend that he does. 

He gravitates to the side of the room, shuffling slowly until he reaches the wall and its from there that he spots Jessica. 

She is sitting sadly on the stairs, head held in her hands. When he approaches her she looks up and sighs deeply.

“Hi Cas.” She says. 

“Jess,” he replies, sitting next to her on the step, “Are you okay?”

“Sam went off with Lucifer.” She says and if that’s case Castiel really should find Dean before he does something stupid. 

But instead he places a hand on Jess’s shoulder,”And that bothers you?”

She looks at him like this should have been obvious and nods,”I guess I really just thought Sam and I had something.”

“And now?”

“Now I don't know what to think.” 

She sighs again and drops her gaze to the floor, “You don't have to do it anymore Castiel. This whole dating Dean thing so that Sam can date. It was a dumb thing to ask of you in the first place.”

Castiel agrees with her wholeheartedly but he won't admit out loud that he's actually glad she did. Because getting to know Dean has been the highlight of his senior year maybe even of his entire high school experience. 

“Jess I think you overestimate Lucifer.” He says and she doesnt look up. 

“But worse,” He continues, “You underestimate yourself.” 

This gets her attention. She looks up at him curiously through a curtain of blonde hair and he says, “Sam came here to be with you. Not Lucifer. And I doubt he would have done that if he wasn't at least a bit interested.”

Jess thinks about this.

“Thanks Cas.” She says so quietly he almost doesn't hear her.

“Of course.” He replies, “Now, i suggest you end your moping and find Sam.”

 

Jess thanks him again and leaves to go find Sam but Castiel still has not seen Dean or Gabriel or any familiar face since then. So he stands stupidly in the center of a crowd of classmates and distant relatives waiting for some sort of sign.

A sign that soon comes in the form of a loud commotion in the next room over. There’s a growing crowd of people cheering for someone Castiel cannot see but assumes is Gabriel. So he pushes through the people grumbling apologies on his way to what looks like the kitchen. 

What he finds there is not Gabriel pulling off some ridiculous attention seeking stunt. It's Dean. Standing on the dining room table, wooden spoon in hand, singing into it like a microphone.

He's swaying slightly and the cup in his hand is clearly neither his first drink nor is it empty. 

He's belting out the lyrics to that one song about being too sexy for your shirt and when he reaches that line he actually removes the plaid overshirt he has on. He makes a show of tossing it aside much to the delight of the crowd around him 

And at the front of it all, laughing and clapping, is Lucifer. Castiel doesn't know how but somehow this is his fault. 

Cas pushes his way to the front and grabs Deans hand to get his attention.

“Oh hey Cas!” He greets, pausing mid-song, “I was looking for you.”

“Hello Dean, please get down. You're going to hurt yourself,” Castiel replies.

“No way, this is so much fun, Next song!” Dean shouts and he tries to stand straight but Castiel’s grip on his arm causes him to waiver.

“No Dean. Please get down.”

“Come on Castiel. Let the man sing. Don't be such a spoilsport.” Lucifer calls over the noise and a few voices in the crowd agree with him.

“Lucifer” Cas warns.

“Let him have his fun Castiel, you have to admit he does look pretty sexy up there.”

“Hey fuck you.” Dean shouts, kneeling to point a finger into Lucifer's face.

“Generous offer but I don’t need to be doing both Winchesters,” Lucifer sneers.

Dean draws his arm back as if to punch Lucifer but he's so off balanced that when he throws his punch Lucifer needs only to step aside and let Dean faceplant off the table.

Castiel anticipates this and moves to catch Dean before he hits the floor, helping him off the table to his feet.

“Shows over.” He says mainly to Lucifer but a few others nearby offer various states of drunken boos. 

Dean leans heavily on him and tries to take another swig of whatever is in his cup. 

Castiel swiftly takes it out of his hand and places it on the nearest flat surface they pass on their way out the door.

“Aw come on Cas ‘m not even that drunk give it back.” Dean complains. 

“I think you've had enough,” Castiel argues, placing his hand on Dean's back to steady him.

“Yeah? How many’ve you had?” Dean argues.

“None.” Castiel replies truthfully.

And Dean tries to count none on his fingers.

“Come on, you need fresh air,” says Castiel and he wishes he thought to grab a glass of water before they left the kitchen. 

“Sounds nice.” Dean agrees but his feet still drag as Castiel struggles to support his weight and clear a path to the front door.

Dean seems to notice Castiel having difficulties because he stops short and pushes off Cas, keeping a hand on his shoulder to steady himself.

“Dean-” Castiel starts.

Dean holds up his free hand, “Check this out,” he says.

He brings his hand to his mouth and clears his throat loudly, “Move!” he shouts, “Gonna puke!”

And Castiel has never seen this many people move so fast. There’s a clear path to the door in seconds.

“Works every time,” Dean says proudly, slumping back against Castiel.

They’re out the door in seconds and Cas is honestly impressed. It could have been hours before he would have been able to get them out of the house. 

He walks Dean across the street to the small community playground, sitting Dean on one swing before taking the one next to it. Dean tilts back precariously and Castiel has his hands up and ready to catch him should he fall again. But Dean doesn’t fall, instead he glances over at Cas and grins.

“You totally thought I was going to tip over just then.” He says like he’s just caught Castiel being foolish.

“Well you’re very drunk Dean.” Castiel reasons.

“Please Cas I’m not that bad,” Dean rolls his eyes and grips the chains on the swing, “Air is nice though, thanks for that.”

“You’re welcome,” Castiel says, then although there’s a part of him he thinks probably doesn’t want to know he asks, “How many did you have?”

“Six?” Dean answers with another question, “I don’t know, I lost count after Lucifer left with Sammy.”

Castiel sighs, “If it’s any consolation, Sam was nowhere near Lucifer when I found you.”

Dean shrugs but doesn’t say anything, his hands drop to his lap and he kicks at the woodchips beneath their feet.

“Why do you let him get to you?” Castiel asks quietly..

“Its not- I just-” Dean turns to face him, pausing to think before trying again, “It's the way he looks at me you know? The way he talks to me. Like I’m not a whole person in here just a nice face and a nicer ass,” he says, laughing a little before continuing on, “And it’s worse with Sam. It’s okay for him to treat me like that but Sam doesn’t deserve it. He’s my little brother Cas and it’s my job to watch out for him, you know? Take care of him. And I won’t let Lucifer manipulate him or treat him like less than a person.”

“It’s not okay for him to treat you like that Dean.” Castiel says as soon as Dean stops talking, “Why would you think that?”

Dean shakes his head, “It’s not like he's the only one who does it. In case you didn’t know I’m not the top of the class. Lucifer’s just the only one brave enough to make it obvious to my face.”

“Is that why you don’t date?” Castiel asks because he truly doesn’t believe John Winchester is the only thing stopping Dean.

“I date.” Dean frowns, “I would date.”

“But you don’t.” Castiel points out.

“Is that illegal or something?” Dean asks defensively.

“No.” Cas says, “I guess not.”

But it does send a wave of disappointment through Castiel although he won’t say it out loud.

“Hey,” Dean grabs Cas’s sleeve and pulls their swings closer together, “I would date. If I met the right person. If I was sure.”

Castiel nods, “Just promise me,” he says, “That when you do meet someone, they treat you like a whole person. You deserve at least that much.”

Dean remains quiet, staring up at Castiel, his face unreadable as he leans against the chain of his swing. There’s a redness on his cheeks from the alcohol illuminated by the near full moon hanging high in the mid night sky. The way it shines on Dean's hair makes his head look like its surrounded by a soft glow, a halo of sorts. His face is so close Castiel could count his freckles if he wanted and Castiel swallows hard, trying to fight back the butterflies he feels in his stomach at that thought.

“Your eyes are really blue.” Dean says casually unaware of the effect his words have on the now rioting butterflies in Castiel’s stomach.

He nods stiffly, “Thanks Dean.”

Deans eyes follow Castiel’s, and Cas gets the feeling it’s useless trying to pretend he’s not flustered. Dean can see right through him anyways.

"You kinda want to kiss me right now don't you?" Dean guesses, his head tilted slightly.

And he’s right. Castiel wants to kiss him. He really does. 

His lips are right there. He’s smiling even.

But there's a look in Deans eyes that Castiel isn’t even sure Dean knows he has. It let’s Castiel know he is being tested and if he fails the test he'll be like any other person in this stupid high school to Dean. And Cas doesn't want   
to be just anyone else to Dean. 

So he forces himself to tear his eyes away from Deans before he does something stupid, standing abruptly and brushing off his pants even though there's no dirt on him. The swing jerks clumsily behind him as he stands and the sounds of metal chains rubbing together cuts through the quiet, effectively ruining the moment.

Dean watches him in surprise, eyes wide. Then he laughs. And it's the first real laugh Castiel has gotten from him. It's a nice laugh, Castiel thinks,and it almost makes up for the fact that he didn't get to kiss him. Almost.   
"You really are something else," Dean says.

And Castiel doesn't know whether to take it as a compliment or an insult. 

But it’s too late to ask because Dean is throwing up.

**Author's Note:**

> Thanks for reading! Hope you enjoyed! Wow, sorry this was so long! Might split this into two parts later depending on public opinion lol.


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